Driven by Taxes

EXPERTS OFTEN ARGUE that tax-avoidance strategies shouldn’t drive our financial plans, especially as Congress is forever fiddling with the tax rules. And yet many of us end up making decisions based on federal tax policy, which is loaded with incentives designed to change behavior and advance social goals.

That’s certainly true for my wife and me. Despite the tax code’s many provisions—and its 75,000 pages of complexity—four big-picture tax considerations have largely shaped how our financial lives have turned out, and perhaps that’s true for you, too.

Homeownership. Tax policy has long encouraged homeownership through the deductions for mortgage interest and property taxes. Before the standard deduction doubled in 2018, some 30% of taxpayers claimed these two deductions.

Homeownership was such a strong pull for my wife and me that we bought our first house in 1979, when we were both age 23, just 10 months after we married. We finagled our finances so we could amass (just barely) the house down payment and meet the monthly mortgage payment.

Subsequently, we bought homes in 1991 and 2022, both of which we still own. Each was a colossal stretch, leaving us cash-strapped for a time. In past decades, buying “the most house you can afford” was common advice to capture both big-dollar tax deductions and the potentially outsized gains from leveraged home-price appreciation.

The 2017 tax law trimmed the use of home-related tax deductions. Today, just 11% of taxpayers take the mortgage interest and property tax deductions. That’s why most financial pundits now recommend against stretching to buy housing. This could change, though, should the 2017 tax law be allowed to sunset as scheduled in 2026 and the standard deduction revert to its earlier, lower levels.

While we now forgo the twin housing tax deductions, we have no plans to change our overweighted real estate holdings, particularly since the latest house purchase is near our children—life’s best tax deduction.

Contributions to 401(k)s. Income saved in our 401(k) plans—along with the subsequent growth of those dollars—are tax-deferred until withdrawn. This led us to accumulate nearly 90% of our financial assets inside tax-deferred accounts by the time we retired. Our lopsided allocation arose because we contributed the maximum to our 401(k) plans each year, while maintaining a 100% stock allocation and never trading in these accounts.

Our retirement savings blossomed, but our finances lacked tax diversification. All this money will be taxed as ordinary income upon withdrawal, not at the lower capital-gains tax rate. The upshot: We have a large pending tax obligation that’ll be paid as we tap these accounts. We’re also handcuffed to the ever-changing rules on required minimum distributions and withdrawals from inherited IRAs.

Unfortunately, our required minimum distributions will be taxed at higher rates than we would have paid when we deferred taxes on contributions during our early working years. We naïvely followed the conventional wisdom that “your tax bracket will be lower in retirement.” We and our advisors never contemplated the potential for tax bracket creep in retirement, the result of decades of inflation and investment appreciation.

Young workers in their lowest tax-rate years are now advised to favor Roth contributions over traditional tax-deductible retirement accounts. Roth and health savings accounts can slow tax-bracket creep for those likely to have higher retirement incomes as a result of career growth, stock appreciation, business income or an inheritance.

Retirees also shouldn’t lose sight of the possibility that their nest egg might double in value should they delay withdrawals for the 10 or 15 years between retirement and the onset of required minimum distributions, currently set at age 73. This could push them into a higher bracket just as the time comes for mandatory taxable distributions.

Step-up in basis. The chance to get embedded capital gains forgiven upon our demise has resulted in our death-grip hold on 19 individual stocks, which we purchased decades ago within our taxable accounts. These highly appreciated stocks are our only remaining after-tax holdings. Each has an unrealized capital gain of between 300% and 10,000%, and together constitute about 12% of our financial assets.

Over the years, we sold all losing stocks to offset realized taxable gains. We also sold any stocks and funds having modest gains to raise cash for, among other things, our 2022 house purchase.

The step-up in cost basis is also one of the main reasons we’ve retained our 1991 house. It’s a complicated situation, but this house has now become an unanticipated furnished rental property. We helped a military family displaced by a fire with a brief emergency rental, which extended into an 11-month stay.

Roth conversions. The lower income tax rates created by the 2017 Tax Cut and Jobs Act prompted us to undertake significant Roth conversions in recent years. Our conversions have been taxed at a 24% federal rate, rather than the 28% or 33% hit that would have been triggered before the 2017 law.

After we cover normal living expenses and help our children a bit, paying the taxes on Roth conversions, plus the resulting higher Medicare premiums, has soaked up every spare penny of after-tax income. Thus far, we’ve converted around 14% of our portfolio to Roth accounts.

Our tax-deferred balances now comprise a less-lopsided 74% of assets, not 90% as before. We plan to continue Roth conversions until the Tax Cut and Jobs Act sunsets in 2026, and possibly until our required minimum distributions start in 2028.

As I look back on the four big tax influencers, tax incentives drove us to overspend on housing and over-save in tax-deferred accounts. Both are considered desirable outcomes from a federal policy viewpoint.

So, too, are our Roth conversions, which have helped fatten the Treasury Department’s tax collections. The anticipation of a step-up in cost basis in our estate has led us to be “forever owners” of stock winners in our taxable account. Yes, despite what the experts advise, we are behavioral slaves to the tax code.

John Yeigh is an author, coach and youth sports advocate. His book “Win the Youth Sports Game” was published in 2021. John retired in 2017 from the oil industry, where he negotiated financial details for multi-billion-dollar international projects. Check out his earlier articles.

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